Perhaps there’s already too much on your to-do list while in Bend, Oregon. Add snow & sunshine and the number of potential adventures increases exponentially. Still, we are making it our mission to discover and share ideas, tips, and new suggestions for making the most of Winter in Bend. Below is an inaugural list, the first in a series that we consider a work in progress.

To get things started, we’ve asked for the input of a few bloggers, friends and generally awesome people to share their #HowToBend tips. Without further ado, we present the first five tips to Bending your Winter.

1. The word is out, if one wishes to get That Pow in Bend, a snowmobile is compulsory.  And oh so cool. The problem is, learning to use it in a way that won’t keep you from ever actually skiing… Don’t ask me, I was hoping you’d know how not to fall off… ~Adam Craig

 backcountry skiing



For another type of sledding adventure check out the Oregon Trail of Dreams, owned and operated by Jerry Scdoris and his daughter Rachael, a world renowned athlete and Iditarod finisher. Plan ahead to enjoy the beauty of Mt. Bachelor guided by a professional musher and a dog sled team.


2. Kayaking in December? Don’t forget your Christmas lights. ~ Luke at

Christmas Kayak Parade returns in December

The Annual Christmas Kayak Parade | December 13, 20











You’re invited to embark on one of Bend’s unique holiday adventures by decorating your craft and joining in the Annual Christmas Kayak parade on December 13th. Tumalo Creek Kayak & Canoe provides all of the details here.


3. Winter running is not only fun, but can be an ideal workout. Just make sure you are prepared to traverse the icy roads and trails with traction – basically, chains for your feet. Local outdoor gear stores like REI carry traction devices that easily strap to shoes of all styles and sizes. And promise us that once your feet are equipped, you won’t forget the rest of your body. ~ Amy Clark at

cassondra schindler singletrack

Our trails love a little traction


December 7th marks the 22nd year of the Jingle Bell Run, a festive fun run where racers of all ages raise money for the Arthritis Foundation. Participants run or walk the 5 kilometer route or 1-Mile route with their team members and celebrate the season by giving to a great cause.


4. Our dogs get dressed up to go out too! We love our pups in Bend and naturally, we share an affinity for gear with our furry friends.

Ruffwear & Ben Moon Photo

©Ruffwear + Ben Moon Foto


Around here, there’s so many places for your pooch to play. Check out the Bend Park & Recreation dog park in the Old Mill District and for a lengthier leashed run, explore River Trail access along the scenic banks of the Deschutes.

5. Bend is the perfect place for reflection. ~ Jen Floyd 

Cyclocross Racing in the Old Mill District

Cyclocross returns to the Old Mill District December 7 & 8















Cyclocross returns to the Old Mill District on December 7th for the Deschutes Brewery Cup followed up by the final Cross Crusade race of the 2103 season on December 8th. With racing categories for all ages, the Cross Crusade events never fail to entertain and inspire your next two wheeled adventure. Bonus tip: don’t let the racing revelry fool you, these athletes are putting everything out there for a strong finish. And they always, always enjoy your encouragement.


Thanks again to our How To Bend Winter contributors Adam Craig,  Luke Menasco, Amy Clark, and Jen Floyd  for their ideas. What would you add to this list? Share #HowToBend Winter by sharing your suggestions in the comments or tagging us @OldMillDistrict on Twitter, Instagram and Facebook. We’ll be announcing weekly winners and sweet rewards.